Iodine → 2,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitol

HRID 1450340Notes

Reaction equation

HRID 1450340 reaction equation
[CH3:1][C:2]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][CH2:7][CH:8]([OH:14])[CH:9]([OH:13])[CH2:10][CH:11]=[CH2:12])([CH3:4])[CH3:3].C(=O)(O)[O-].[Na+].[I:32]I>C(OCC)C.O>[CH3:4][C:2]([Si:5]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:6][CH2:7][C@H:8]1[O:14][C@H:11]([CH2:12][I:32])[CH2:10][C@H:9]1[OH:13])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 807IodineHCID 516892Sodium BicarbonateHCID 220709881-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diol

Product 1

HCID 677073192,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitolYield 76.3%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

A 0° C. solution of 14.67 g of product from Example 274 in 200 ml of 3:1 diethyl ether/water is treated with 4.99 g of sodium bicarbonate and 15.07 g of iodine. The reaction mixture is stirred vigorously for 24 hours at room temperature, quenched with 15 ml of saturated sodium sulfite, and diluted with 100 ml of water. The reaction mixture is extracted with diethyl ether, dried, concentrated in vacuo, and purified by chromatography (silica gel: 0-10% ethyl acetate/hexane) to give 15.0 g of the desired product.

Workup

  1. customquenched with 15 ml of saturated sodium sulfite
  2. additiondiluted with 100 ml of water
  3. extractionThe reaction mixture is extracted with diethyl ether
  4. customdried
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography (silica gel: 0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-90c93ad246f048a6b936035d99b6e8fa
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Reaction notes

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